


Baggy Sweatshirts and Plaid Miniskirts

by HalfwayToHell



Series: American Sweetheart [3]
Category: Supernatural RPF
Genre: Alternate Universe - Student/Teacher, Explicit Thoughts, Feminization, M/M, Masturbation, Sex Toys, Teacher-Student Relationship, Vibrator, Webcam/Video Chat Sex, college professor!Jensen, college student!Jared
Language: English
Status: Completed
Published: 2016-08-30
Updated: 2016-08-30
Packaged: 2018-08-11 08:08:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,033
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7883329
Author URL: https://archiveofourown.org/users/HalfwayToHell/pseuds/HalfwayToHell
Summary: <blockquote class="userstuff">
              <p>After weeks of examining Jared, Jensen felt he was barely scraping the surface of a much bigger picture. When Jared does the unthinkable and approaches him of his own will, Jensen's dark desires run rampant inside of his mind and he can't help himself but wonder. Existing in two different fantasy worlds inhabited by the boy on the webcam and his new student, Jensen finds himself conflicted between the two--equally wanting them both as his own. A misplaced piece of evidence will lead Jensen to realize that the boy on the webcam and Jared are both the same people but different in their own unique way. In the end, Jensen swears that he will have them both as his own.</p>
            </blockquote>





	Baggy Sweatshirts and Plaid Miniskirts

**Author's Note:**

> Official American Sweetheart Playlist:
> 
> Stevie Nicks- Has Anyone Ever Written Anything For You  
> Angus & Julia Stone- You’re The One That I Want  
> Cold Specks- Winter Solstice  
> Nicole Dollanganger- Flowers Of Flesh And Blood  
> Noah Gundersen- Slow Dancer  
> Ben Harper and the Innocent Criminals- Goodbye To You  
> Lacey Sturm- Run To You  
> The Lumineers- White Lie  
> Hearts & Colors- Lighthouse (Acoustic version)  
> Shawn Mendes- Mercy  
> The Strumbellas- I Still Make Her Cry  
> The Strumbellas- The Night Will Save Us

                                                         

* * *

 

In only a few short weeks, Jensen felt as though he was barely starting to scratch the surface where Jared was concerned. The boy was as mysterious as he was predictable and that conundrum alone caused Jensen turmoil. He wasn’t much for puzzles—and he was known to avoid them as much as he deemed necessary even if it was something as insignificant as leaving the Sudoku blank on his Sunday papers—but there was something about Jared that made him want to take him apart and piece him back together again, to find out what truly makes the boy tick—even if that meant sticking him beneath a microscope.

 

What Jensen knew about his student was this:

 

Every day Jared wore a jacket or a sweatshirt—each a size too big for his small frame—and his beaten up black Converse. It was no different today when he showed up in a burnt orange sweatshirt with the phrase UNIVERSITY OF TEXAS AT AUSTIN in bold letters printed across his chest in white and his Converse scuffed across the floor when he walked.

 

And just like every day, Jared sat in the same spot, in the same chair located only feet away from Jensen’s desk. He would sit with his arms folded across the top of the desk, leaning all his weight forward onto his arms and he would chew on the end of a mechanical pencil or a pen as he listened to Jensen’s lecture each Tuesday and Thursday morning.

 

Every day as Jared would gather up his textbooks and backpack, there was always a moment where the boy seemed to pause—as if he was considering something other than his next class for that brief moment—but he never stayed longer than a few minutes after class.

 

Today, Jared had done the unthinkable as Jensen happened to glance up from the paperwork laid out on his desk:

 

The boy approached him.

 

Jared was timid at first—clutching his books to his chest as if they were the only things anchoring him to Earth and his knuckles were bone white from how hard he was gripping the precious pieces of literature—as he first advanced toward Jensen’s desk.

 

Had Jensen not glanced up initially, he would not have noticed the boy as he stood a mere foot away from the edge of his desk. There was a moment—a fleeting flicker of emotion in the boy’s kaleidoscope eyes—where he was sure that Jared was going to abandon his original mission. To say that Jensen was surprised when Jared shuffled even closer to him would be a foolish understatement.

 

“Jared,” Jensen acknowledged him with a light smile, masking the astonishment in his voice. “What can I do for you?”

 

The boy’s tongue flicked out to lick his bottom lip before his teeth caught onto the plush of his mouth—a sign of anxiety. Jared fidgeted for a moment, his eyes avoiding Jensen’s unknowingly intense gaze before he forced himself to stare at his instructor.

 

“I know you said that our next essay wasn’t due for another week or so, but--” Jared took in a deep bracing breath. “I don’t think I completely understand the requirements. I mean, I’ve read and I understand the short story that we’re writing our next analysis on, but I am not one-hundred percent sure--”

 

“On how you’re supposed to write your analysis,” finished Jensen, unable to hide the widening of the grin on his face as he watched the boy squirm—his innocence tasting sweet on his tongue.

 

Jared gave a quick nod, his bangs falling into his eyes.

 

“Luckily, you’ve caught me on a good day. I won’t have my board meeting for another hour,”—At this, a smile crept across Jared’s lips, and there was a faint hint of dimples creasing in his cheeks— “So pull up a chair and I’ll try to the best of my ability to answer your questions as fully as I can.”

 

Jensen watched in anticipation as the boy pulled up the only chair—other than his own—in the entire room that was not bolted to a desk. Jared was sitting so close, invading so much of his personal space, that Jensen could feel the heat from the boy’s body caress his own. Their knees were mere inches apart from one another.

 

This was the closest Jensen had ever been to Jared and because of their close proximity, it was taking his mind a moment to fully register. Jensen had always wondered—always day dreamed—about being this close to Jared. Although admittedly, there was an underlying of shame when he thought about the boy in ways that he shouldn’t.

 

He thought about how _easy_ it would be to pull the boy in, to press his mouth against Jared’s, to intertwine his fingers in the soft strands of his chest nut colored hair. How _effortless_ it would be to manhandle the boy in any way he so desired. How _painless_ it would be to bend the boy over his desk—or perhaps allow him to be sprawled on his back atop his desk—and whisper filth in his ears. How _simple_ it would be to make the boy squirm beneath him, make the boy whimper his name and beg for him. How _natural_ it would be for him to sink himself into the warm, tight heat of the boy’s body. And finally, how _uncomplicated_ it would be for Jensen to give in to Jared’s wants and desires.

 

Whether Jensen wished to admit it or not: his will was weak where Jared was concerned.

 

Being this close to the boy, he could smell a faint fragrance from his sweatshirt—a cologne of sort was Jensen’s initial thought until he breathed in deeper. The scent had floral notes with sweet undertones—most certainly not a fragrance associated with men’s cologne.

 

The oddly feminine scent wafting off the boy was not the only strange details he realized being this close. Jared’s hands were slender and his fingers even more so, but it was not the delicate nature of the boy’s hands that caught his attention—it was the fragment of color up near the cuticle of the boy’s nails. It was a flake of pink, like the last remaining chip of color on a woman’s nails where she had not been able to fully remove all of the polish from her hands.

 

Aside from the out of place pink sliver, Jensen noticed the length of the boy’s nails. They were longer than what most men would keep them, but not quite as long as what a typical woman would keep her nails as and it wasn’t just that either—it looked as if the boy took a particular interest in the special care of his nails, more so than any man should or would care to.

 

If Jensen had paid careful attention to details, he would have pieced the puzzle together a lot sooner than he initially did—remember, he wasn’t one for enigmas—but the despondent reality of it all was that he had not.

 

Instead, Jensen pushed the peculiar details aside and focused all his attention on the task at hand.

 

The next forty-five minutes passed by in such an incomprehensible blur, that Jensen could not copiously recollect what the boy had asked him or what he had said to him, or if he had spoken much at all. Before he had known it, Jared was packing up his books into his bag, repetitively thanking Jensen for his assistance.

 

“If you ever need anything—anything at all—I ask that you do not hesitate to come to me, understand, Jared?” Jensen requested as he rose from his chair.

 

Jared smiled up at him as he slung his backpack over his petite shoulders and the cheerful glimmer in the boy’s eyes caused heat to stir in the lowest pit of Jensen’s gut.

 

“Yeah. Of course.”

 

“Good. Oh, and one last thing before you go, have you thought of your answer yet?”—At this, a tenuous V shape appeared between the boy’s eyebrows— “What is it about you that makes you interesting?” Jensen clarified.

 

The same nervous ticks as before when Jared was initially questioned surfaced once more. He bit his lower lip until Jensen was sure he would bite right through it and he avoided eye contact as if he had been beaten severely for a numerous amount of times.

 

“I can play the piano,” answered Jared at last, turning his attentive gaze back onto Jensen.

 

“Can you?” Jensen folded his arms across his chest, his interest in the boy’s extra-curricular activity to be genuine. Jared offered a small nod. “Where did you learn to play?”

 

“My mother. When I was growing up she used to offer private piano lessons after school to help pay the bills. On days that she didn’t have any students scheduled she’d teach me,” He explained as his fingers played with the simple leather cord around his throat.  

 

“Do you have a favorite piece that you play?”

 

There was a guarded edge to the boy’s eyes, something Jensen had not seen up until that very instance.

 

“The very first song I learned to play was _Moonlight Sonata_ ,” Jared replied after another long pause, another calculated answer—another reply that made Jensen want to take the boy apart and piece him back together again. “but the song I’ve been playing a lot lately is _Nuvole bianche_ by Ludovico Einaudi.”

 

To say that Jensen was astounded by the articulacy of the boy’s pronunciation would not give it justice.

 

“Sounds like I might need to expand my music collection,” said Jensen as he walked Jared over to the door and the whole way over, the boy could not keep the gentle smile nor the dimples in his cheeks a secret. “Have a great weekend, Jared.”

 

A faint hue of pink touched the boy’s cheeks and he averted his gaze, his eyelashes casting a shy shadow. “You too, Mr. Ackles.”

 

♥  ♥  ♥  ♥

 

Music flowed through his veins and pooled in his heart.

 

His eyes were closed as he reclined back in his office chair, his hands folded in his lap as he allowed the somber tune to crash over him.

 

Jensen could not count on both of his hands or his feet how many times he had listened to the beautifully dismal song that Jared had mentioned. He had found the song on the internet being played and recorded by the pianist.

 

The more he listened, the more he allowed the melody to take hold of him, he began to realize that the song was not entirely despondent. There were parts where it was fast and joyful and it all clicked in:

 

The song was a representation of life itself.

 

Jared had a clever taste in music, that Jensen was sure of.

 

While he listened, Jensen envisioned Jared’s slender fingers dancing across the ivory keys, plucking the tune that rushed through his veins.

 

Of course over the past couple of weeks he had imagined Jared in every way conceivable—his small back arching up off his bedsheets, his slender thighs trembling while he was between them, his hands and nails clawing at the expanse of his own back and shoulder blades, the way a light sheen of sweat would collect at the base of the boy’s throat and collarbones, and the delightful sounds that would escape from his quivering mouth while he was buried cock deep in him—but envisaging him this way was his favorite.

 

And perhaps Jensen felt that way because this was something personal about the boy, something that he had permitted him to know. He wondered then what Jared would look like playing a piano. If his eyes would be closed or if he’d sway a little in time with his key strokes or if he’d hum the tune beneath his breath or if he did not need any sheet music because he had them all memorized.

 

Jensen wanted to know this intimate yet seemingly innocent detail about Jared as much as he wanted to know other private aspects about him.

 

The familiar ding from his laptop forced his eyes open, disrupting the bliss he had been in moments prior. He leaned forward in his chair and pressed a key to bring his screen to life once more.

 

  * **BUBBLEGUM BITCH:** _Hello, Mr. Ross. What can I do for you today?_



 

The boy on the other end of the webcam sat with his ankles crossed, his black stocking clad legs dangling off the edge of his bed. The boy wore a pleated miniskirt this time—although Jensen was not sure if he would classify it as a skirt really, more or less like a hunter green piece of fabric chased through with stitching of blue and gold plaid—with a long-sleeved charcoal gray cable knitted sweatshirt.

 

It was an outfit customary to a prestigious Catholic schoolgirl.

 

The boy’s nails were painted a glittery black—causing his hands to look even more willowy and porcelain pale than normal—as he played with the collar on his sweatshirt, awaiting Jensen’s reply.

 

  * **ROSS:** _Since you’ve been such a good girl for me, I’ll let you decide, sweetheart._



 

A vixen smile graced the boy’s daintily glossed lips as he slid from the bed, disappearing only for a moment before he came back into the webcam’s view. The boy removed the sweatshirt from his body in one quick motion and hiked the skirt up farther onto his hips.

 

Normally, Jensen’s eyes would have fell where the boy’s hand was currently holding a small, egg-shaped vibrator in his hand as he stroked his cock. But this time was anything but normal.

 

A thin leather cord laid snug against the boy’s throat and Jensen’s breath caught in his chest cavity. It was the very same cord he had seen Jared wear, the very same one that he would finger during his class lectures.

 

Jensen wanted to believe that it was a coincidence, but he could not make himself believe so. After all, the boy on the webcam and Jared already had so many similarities that were gradually coming to the surface the longer Jensen stared at the boy, the longer he inspected him.

 

They had the same slender body type and the same height. They both had slim hands with long fingers that were perfect for playing the keys on a piano. Their noses were both lean and upturned and the spot where the boy always drew a heart shaped mark in black eyeliner covered the very same place where Jared’s natural beauty mark was.

 

There were far too many correspondences for Jensen to convince himself that this boy was not Jared.

 

The fact that this boy had a fairly high chance of being Jared—the soft, sweet, shy boy from his class—caused a groan to come from the back of his throat as he palmed at his aching cock through his slacks.

 

The boy’s teeth dug into his bottom lip as his hand that held the vibrator against his cock stroked faster, his hips grinding up desperately into his palm and a pearl shaped amount of pre-come bubbled onto the head. His body shook as his orgasm built and his head was tossed back, exposing the curve of his throat that was protected by the leather cord.

 

The boy’s body suddenly seized, the muscles in his lower abdomen flexing as he came—a cry falling past his lips.

 

Jensen’s own boxers suddenly felt warm and sticky as he realized that he too was taken over by an orgasm that he was far too preoccupied to notice taking place. His mouth was dry as he watched the boy recompose himself, cleaning the white mess from his hand with a spare hand towel.

 

  * **BUBBLEGUM BITCH:** _Is there anything else I can do for you, Mr. Ross?_



 

Naturally, Jensen would have immediately answered with asking the boy for his name, but this time Jensen was sure that he already knew who he was.

 

It had to be Jared.

 

It just _had_ to be.

 

This Jensen was sure of.

 

  * **ROSS:** _Would you be willing to go to dinner with me this Saturday night?_



 

The stillness that came over the boy then caused Jensen’s heart to beat in his throat. For a moment, he was sure the boy would suddenly disconnect and that was a risk that Jensen couldn’t take. Not now.

 

  * **BUBBLEGUM BITCH:** _Even if we lived in the same town, I don’t meet my clients in person and I don’t have sex with them either. It’s not safe. Besides. I doubt you live in the same town that I do. I live in Austin, Texas._



 

  * **ROSS:** _What if I paid_ you _double? I’m not asking for sex, sweetheart. I would just like to meet you. Even if it is only once. I reside in Austin as well._



 

He watched with his hope dangling by a fragile thread as the boy bit his bottom lip, mulling the idea over. Jensen could hear the thoughtful taps of the boy’s fingers against the keyboard of his laptop as he thought the proposal over.

 

  * **BUBBLEGUM BITCH:** _Fine. But just dinner. That’s it._



 

Jensen could not hide the triumphant grin that curled at the corner of his mouth.

 

  * **ROSS:** _Just dinner. I promise. How does eight o’clock at Eddie V’s sound?_



 

  * **BUBBLEGUM BITCH:** _I’ll see you then, Mr. Ross. I’ll be the one wearing pink._



 

  * **ROSS:** _And I’ll be the one wearing a tie. May I get a name for the reservation?_



 

  * **BUBBLEGUM BITCH:** _Tristian. Have a good night, Mr. Ross. I will see you tomorrow at Eddie V’s._



 

And with that, the boy that had been the main topic of his dark desires signed off of the webcam for the night. Jensen leaned back in his chair, trying to slow the quickness of his heart. There was a part of him that was overjoyed that he was going to finally meet the boy over the webcam, but that did not help the sickening twist in his gut as a thought occurred to him for a moment:

 

What if he was wrong?


End file.
